Cycloate, an inhibitor of fatty acid elongase, modulates the metabolism of very-long-side-chain alkylresorcinols in rye seedlings

Pest Management Science

Volumn 65, Issue 10, 2009, Pages 1065-1070

  Magnucka, Elzbieta G ^a   Suzuki, Yoshikatsu ^b   Pietr, Stanislaw J ^a   Kozubek, Arkadiusz ^c   Zarnowski, Robert ^d  

^a WROC AW UNIVERSITY OF ENVIRONMENTAL AND LIFE SCIENCES   (Poland)

^b INST OF PHYS AND CHEMICAL RESEARCH   (Japan)

^c UNIVERSITY OF WROC AW   (Poland)

^d UNIVERSITY OF TEXAS PAN AMERICAN   (United States)

Author keywords

Cycloate; Herbicide; Secale cereale

Indexed keywords

ACYLTRANSFERASE; CYCLOATE; ENZYME INHIBITOR; FATTY ACID; FATTY ACID ELONGASES; HERBICIDE; THIOCARBAMIC ACID DERIVATIVE; VEGETABLE PROTEIN;

ALIPHATIC HYDROCARBON; CEREAL; CHEMICAL CONTROL; ENZYME ACTIVITY; FATTY ACID; HERBICIDE; LIGHT EFFECT; METABOLISM; MICROBIAL ACTIVITY; PATHOGEN; PLANT DEFENSE; PLANT PRODUCT; SEEDLING; TEMPERATURE EFFECT;

ARTICLE; CHEMISTRY; DRUG ANTAGONISM; DRUG EFFECT; ENZYMOLOGY; METABOLISM; RYE; SEEDLING;

ACETYLTRANSFERASES; ENZYME INHIBITORS; FATTY ACIDS; HERBICIDES; PLANT PROTEINS; SECALE CEREALE; SEEDLING; THIOCARBAMATES;

SECALE CEREALE;

EID: 70349643382     PISSN: 1526498X     EISSN: 15264998     Source Type: Journal    
DOI: 10.1002/ps.1792     Document Type: Article

References (40)

1. Ahrens W, Herbicide Handbook. Weed Science Society of America, Champaign, IL (1994).
2. Fang SC, Thiocarbamates, in Herbicides, Chemistry, Degradation and Modeof Action, ed. by Kearney PC and Kaufman DD. Marcel Dekker, New York, NY, pp. 328-348 (1975).
3. Onisko BC, Barnes JP, Staub RE, Walkr FH and Kerlinger N, Metabolism of cycloate in radish leaf: metabolite identification by packed capillary flow fast atom bombardment tandem mass spectrometry. Biol Mass Spectrom 23:626-636 (1994).
4. Kosinkiewicz B, Wegrzyn T, and Pietr SJ, Interaction between bacterial metabolites and some pesticides. II. Change of phytotoxicity of the herbicide Roneet by the phenolic metabolites of Arthrobacter sp. Acta Microbiol Polon 33:111-117 (1984).
5. Gronwald JW, Lipid biosynthesis inhibitors. Weed Sci 39:435-449 (1991).
6. Von Wettstein-Knowles P, Biosynthesis and genetics of waxes, in Waxes: Chemistry, Molecular Biology and Functions, ed. By Hamilton RA. The Oily Press, Dundee, UK, pp. 91-129 (1995).
7. Barrett PB and Harwood JL, Characterization of fatty acid elongase enzymes from germinating pea seeds. Phytochemistry 48:1295-1304 (1998).
8. Post-Beittenmiller D, Biochemistry and molecular biology of wax production in plants. Annu Rev Plant Physiol Plant Mol Biol 47:405-430 (1996).
9. Kerstiens G, Signalling across the divide: a wider perspective of cuticular structure-function relationship. Trends Plant Sci 1:125-129 (1996).
10. Still GG, Davis DG and Zander GL, Plant epicuticular lipids: alteration by herbicidal carbamates. Plant Physiol 46:307-314 (1970).
11. Kolattukudy PE and Brown L, Inhibition of cuticular lipid biosynthesis in Pisum sativum by thiocarbamates. Plant Physiol 53:903-906 (1974).
12. Harwood JL and Stumpf PK, Fat metabolism in higher plants. XLIII. Control of fatty acid synthesis in germinating seeds. Arch Biochem Biophys 142:281-291 (1971).
13. Baldwin A, Rogers HJ, Francis D, and Harwood JL, Fatty acid elongation is important in the activity of thiocarbamate herbicides and in safening by dichlormid. J Exp Bot 54:1289-1294 (2003).
14. Owen WJ, Herbicide metabolism as a basis for selectivity, in Target Sites for Herbicide Actions, ed. by Kirkwood RC. Plenum Press, New York, NY, pp. 285-298 (1991).
15. Barrett PB and Harwood JL, Effects of pebulate and pebulate sulphoxide on very long chain fatty acid biosynthesis. Phytochemistry 48:441-446 (1998).
16. Ramsey RJL, Mena FL and Stephenson GR, Effects of chemical safeners on herbicide action, in Pesticide Biotransformation in Plants and Microorganisms, Similarities and Divergences, ed. By Hall JC, Hoagland RE and Zablonowicz RM. ACS, Washington, DC, pp. 310-332 (2000).
17. Garcia S, Garcia C, Heinzen H and Moyna P, Chemical basis of the resistance of barley seeds to pathogenic fungi. Phytochemistry 44:415-418 (1997).
18. Reiss J, Influence of alkylresorcinols from rye and related compounds on the growth of food-borne molds. Cereal Chem 66:491-493 (1989).
19. Zarnowski R, Kozubek A and Pietr SJ, Effect of rye 5-n-alkylresorcinols on in vitro growth of phytopathogenic Fusarium and Rhizoctonia fungi. Bull Pol Acad Sci Biol Sci 47:231-235 (1999).
20. Droby S, Prusky D, Jacoby B and Goldman A, Induction of antifungal resorcinols in flesh of unripe mango fruits and its relation to latent infection by Alternaria alternata. Physiol Mol Plant Pathol 30:285-292 (1987).
21. Adawadkar PD and ElSohly MA, Isolation, purification and antimicrobial activity of anacardic acids from Ginkgo biloba fruits. Fitoterapia 52:129-135 (1981).
22. Kozubek A, Isolation of 5-n-alkyl-, 5-n-alkenyl- and 5-n-alkadienyl-resorcinol homologs from rye grains. Acta Alimen Polon 9:185-198 (1985).
23. Ross AB, Kamal-Eldin A, Jung C, Shepherd MJ and Äman P, Gas chromatographic analysis of alkylresorcinols in rye (Secale cereale L.) grains. J Sci Food Agric 81:1405-1411 (2001).
24. Deszcz L and Kozubek A, Higher cardol homologs (5-alkylresorcinols) in rye seedlings. Biochim Biophys Acta 1483:241-250 (2000).
25. ′Z-heptadecenyl)-resorcinol from etiolated rice seedlings as an antifungal agent. Phytochemistry 41:1485-1498 (1996).
26. Daniel O, Meier MS, Schlatter J and Frischknecht P, Selected phenolic compound in cultivated plants: ecologic functions, health implication and modulation by pesticides. Environ Health Perspect 107:109-114 (1999).
27. Magnucka E, Zarnowski R, Suzuki Y, Yamaguchi I, Pietr SJ and Kozubek A, The influence of herbicides on biosynthesis of antifungal resorcinols by rye seedlings. Bull Pol Acad Sci Biol Sci 49:361-369 (2001).
28. Magnucka E, Suzuki Y, Pietr SJ, Kozubek A and Zarnowski R, Effect of norflurazon on resorcinolic lipid metabolism in rye seedlings. Z Naturforsch 62c:239-245 (2007).
29. Zarnowski R and Suzuki Y, 5-n-alkylresorcinols from grains of winter barley (Hordeum vulgare L.). Z Naturforsch 59c:315-317 (2004).
30. Kozubek A and Tyman JHP, Resorcinolic lipids, the natural non-isoprenoid phenolic amphiphiles and their activity. Chem Rev 99:1-26 (1999).
31. Kozubek A and Tyman JHP, Bioactive phenolic lipids, in Studies in NaturalProductsChemistry, ed.by Atta-ur-Rahman. Elsevier Science Publishers, Amsterdam, The Netherlands, pp. 111-190 (2005).
32. Suzuki Y, Kurano M, Esami Y, Yamaguchi I and Doi Y, Biosynthesis of 5-alkylresorcinolinrice:incorporation of aputative fattyacidunitin the 5-alkylresorcinolcarbonchain.BioorgChem 31: 437-452 (2003).
33. Funa N, Ozawa H, Hirata A and Horinouchi S, Phenolic lipid synthesis by type III polyketide synthases is essential for cyst ormation in Azotobacter vinelandii. PNAS 103:6356-6361 (2006).
34. Tluscik F, Kozubek A and Mejbaum-Katzenellenbogen W, Alkylresor-cinols in rye (Secale cereale L.) grains. VI. Colorimetric micromethod for the determination of alkylresorcinols with the use of diazonium salt, Fast Blue B. Acta Soc Bot Polon 50:645-651 (1981).
35. Zarnowski R and Suzuki Y, ExpedientSoxhletextractionofresorcinolic lipids from wheat grains. J Food Comp Anal 17:649-663 (2004).
36. Vidal A, Dinya Z, Mogyorodi F, Jr, and Mogyorodi F, Photocatalytic degradation of thiocarbamate herbicide activeingredientsinwater. Appl Catal B Environ 21:259-267 (1999).
37. Lanyi K and Dinya Z, Photodegradation study for assessing the environmentalfateofsometriazine-,urea-andthiocarbamate-type herbicides. Microchem J 80:79-87 (2005).
38. 14C]stearoyl-CoA elongation by etiolated leek seedling microsomes. Arch Biochem Biophys 15:260-269 (1985).
39. Walker KA, and Harwood JL, Evidence for separate elongation enzymes for very-long-chain-fatty-acid synthesis in potato (Solanum tuberosum). Biochem J 237:41-50 (1986).
40. Lemanczyk G and Wasilewski P, Impact of different forecrops on the health status of winter rye stem base. Acta Scient Polon 1:73-81 (2002).